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Solvent-Controlled Pd(II)-Catalyzed Aerobic Chemoselective Intermolecular 1,2-Aminooxygenation and 1,2-Oxyamination of Conjugated Dienes for the Synthesis of Functionalized 1,4-Benzoxazines.

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Pd(II)-catalyzed intermolecular 1,2-aminooxygenation and 1,2-oxyamination of conjugated dienes have been developed. The chemoselective preparation of a variety of 2-functionalized and 3-functionalized 1,4-benzoxazine derivatives was accomplished via the adjustment of a… Click to show full abstract

Pd(II)-catalyzed intermolecular 1,2-aminooxygenation and 1,2-oxyamination of conjugated dienes have been developed. The chemoselective preparation of a variety of 2-functionalized and 3-functionalized 1,4-benzoxazine derivatives was accomplished via the adjustment of a coordinating solvent. Oxygen was successfully used in this oxidative difunctionalization of alkenes. Good yields and selectivities were obtained for most products. A product bearing a spiro structure was also obtained from a 2,3-disubstituted-1,3-diene.

Keywords: intermolecular aminooxygenation; aminooxygenation oxyamination; oxyamination conjugated; conjugated dienes

Journal Title: Organic letters
Year Published: 2018

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